Pelanserin

Pelanserin
Names
	Preferred IUPAC name 3-[3-(4-Phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione
	Other names TR2515
Identifiers
CAS Number	2208-51-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	58898;
PubChem CID	65435;
UNII	6SNR96E409 ;
CompTox Dashboard (EPA)	DTXSID60176578 ;
	InChI InChI=1S/C21H24N4O2/c26-20-18-9-4-5-10-19(18)22-21(27)25(20)12-6-11-23-13-15-24(16-14-23)17-7-2-1-3-8-17/h1-5,7-10H,6,11-16H2,(H,22,27) Key: WPKPLSFHHBBLRY-UHFFFAOYSA-N; InChI=1/C21H24N4O2/c26-20-18-9-4-5-10-19(18)22-21(27)25(20)12-6-11-23-13-15-24(16-14-23)17-7-2-1-3-8-17/h1-5,7-10H,6,11-16H2,(H,22,27) Key: WPKPLSFHHBBLRY-UHFFFAOYAV;
	SMILES C1CN(CCN1CCCN2C(=O)C3=CC=CC=C3NC2=O)C4=CC=CC=C4;
Properties
Chemical formula	C21H24N4O2
Molar mass	364.449 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pelanserin (TR2515) is a chemical compound that acts as an antagonist of the 5-HT₂ and α₁-adrenergic receptors.^[1]

Synthesis

Pelanserin (3) can be synthesized by a reaction between isatoic anhydride (1) and 1-(3-aminopropyl)-4-phenylpiperazine (2) in the presence of phosgene.^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]

References

^ Villalobos-Molina, R; Ibarra, M; Hong, E (1995). "The 5-HT2 receptor antagonist, pelanserin, inhibits alpha 1-adrenoceptor-mediated vasoconstriction in vitro". European Journal of Pharmacology. 277 (2–3): 181–5. doi:10.1016/0014-2999(95)00074-u. PMID 7493607.
^ Hayao, Shin; Havera, Herbert J.; Strycker, Wallace G.; Leipzig, T. J.; Kulp, Richard A.; Hartzler, Harold E. (1965). "New Sedative and Hypotensive 3-Substituted 2,4(1H,3H)-Quinazolinediones". Journal of Medicinal Chemistry. 8 (6): 807–811. doi:10.1021/jm00330a017. PMID 5885076.
^ Havera, Herbert J.; Vidrio, H. (1979). "Derivatives of 1,3-disubstituted 2,4(1H,3H)-quinazolinediones as possible peripheral vasodilators or antihypertensive agents". Journal of Medicinal Chemistry. 22 (12): 1548–1550. doi:10.1021/jm00198a024. PMID 231656.
^ Garcia, J. D.; Somanathan, R.; Rivero, I. A.; Aguirre, G.; Hellberg, L. H. (2000). "Synthesis of Deuterium-Labeled Antihypertensive 3-(4-Phenyl-1′-Piperazinyl)-Propyl-2,4-Quinazolinedione". Synthetic Communications. 30 (15): 2707–2711. doi:10.1080/00397910008086895.
^ . doi:10.5012/bkcs.2011.32.9.3480. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
^ Cortez, R.; Rivero, I. A.; Somanathan, R.; Aguirre, G.; Ramirez, F.; Hong, E. (1991). "Synthesis of Quinazolinedione Using Triphosgene". Synthetic Communications. 21 (2): 285–292. doi:10.1080/00397919108020823.
^ AT 269143B, "Verfahren zur Herstellung von neuen Chinazolindionderivaten und ihrer Säureadditionssalze bzw. ihrer entsprechenden Piperaziniumverbindungen [Process for the preparation of new quinazolinedione derivatives and their acid addition salts or their corresponding piperazinium compounds]", published 1969-03-10, assigned to Miles Laboratories, Inc.
^ Hayao Shin, U.S. patent 3,274,194 (1966 to Bayer Corp)
^ Horacio Vidrio, U.S. patent 3,919,425 (1975 to Bayer Corp).

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[1] Villalobos-Molina, R; Ibarra, M; Hong, E (1995). "The 5-HT2 receptor antagonist, pelanserin, inhibits alpha 1-adrenoceptor-mediated vasoconstriction in vitro". European Journal of Pharmacology. 277 (2–3): 181–5. doi:10.1016/0014-2999(95)00074-u. PMID 7493607.

[2] Hayao, Shin; Havera, Herbert J.; Strycker, Wallace G.; Leipzig, T. J.; Kulp, Richard A.; Hartzler, Harold E. (1965). "New Sedative and Hypotensive 3-Substituted 2,4(1H,3H)-Quinazolinediones". Journal of Medicinal Chemistry. 8 (6): 807–811. doi:10.1021/jm00330a017. PMID 5885076.

[3] Havera, Herbert J.; Vidrio, H. (1979). "Derivatives of 1,3-disubstituted 2,4(1H,3H)-quinazolinediones as possible peripheral vasodilators or antihypertensive agents". Journal of Medicinal Chemistry. 22 (12): 1548–1550. doi:10.1021/jm00198a024. PMID 231656.

[4] Garcia, J. D.; Somanathan, R.; Rivero, I. A.; Aguirre, G.; Hellberg, L. H. (2000). "Synthesis of Deuterium-Labeled Antihypertensive 3-(4-Phenyl-1′-Piperazinyl)-Propyl-2,4-Quinazolinedione". Synthetic Communications. 30 (15): 2707–2711. doi:10.1080/00397910008086895.

[5] . doi:10.5012/bkcs.2011.32.9.3480. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)

[6] Cortez, R.; Rivero, I. A.; Somanathan, R.; Aguirre, G.; Ramirez, F.; Hong, E. (1991). "Synthesis of Quinazolinedione Using Triphosgene". Synthetic Communications. 21 (2): 285–292. doi:10.1080/00397919108020823.

[7] AT 269143B, "Verfahren zur Herstellung von neuen Chinazolindionderivaten und ihrer Säureadditionssalze bzw. ihrer entsprechenden Piperaziniumverbindungen [Process for the preparation of new quinazolinedione derivatives and their acid addition salts or their corresponding piperazinium compounds]", published 1969-03-10, assigned to Miles Laboratories, Inc.

[8] Hayao Shin, U.S. patent 3,274,194 (1966 to Bayer Corp)

[9] Horacio Vidrio, U.S. patent 3,919,425 (1975 to Bayer Corp).

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[2]

[3]

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[7]

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[9]

Synthesis

See also

References